Anyone seen Unforgiven?
That film was the antidote to the Western (yee haa, get off your horse and drink your milk) style morality, of goodies and baddies.
It is cyberpunk, not westerns that fuel IT security, and it is that level of complexity and ambiguous morality that is closer to reality.
It is far too simplistic to see it as black and white, and it is far too interesting to see it as shades of grey :)
It is only the vigilantes who see themselves as cowboys, and hey most of them are angling for jobs at MS. The west was not won by the cowboys, no matter how many times you may watch True Grit, it was won by the Pinkerton Detective Agency, basically a private army. Messrs Sundance and Cassidy never stood a chance.
IT security has virtually no good guys, it is just about people protecting their space, and others trying to invade, with arms suppliers on both sides. There is a grungy appeal to it all, but basically it revolves around poking your nose into other people's affairs or giving someone else a really shitty day, normally both :)